KR20160127428A

KR20160127428A - An electroluminescent compound and an electroluminescent device comprising the same

Info

Publication number: KR20160127428A
Application number: KR1020150058825A
Authority: KR
Inventors: 현서용; 정성욱
Original assignee: (주)피엔에이치테크
Priority date: 2015-04-27
Filing date: 2015-04-27
Publication date: 2016-11-04
Also published as: KR101891714B1

Abstract

The present invention relates to an organic light-emitting compound, applied to an organic electroluminescent device. The organic light-emitting compound is represented by chemical formula 1. The organic electroluminescent device having excellent light-emitting properties such as a driving voltage, brightness, a long lifespan, and the like can be performed in the case of applying the same to an organic matter layer of the device.

Description

TECHNICAL FIELD The present invention relates to an organic electroluminescent compound and an electroluminescent device comprising the same,

The present invention relates to an organic light emitting compound, and more particularly to an organic light emitting compound which is employed as a host compound or a dopant compound in a light emitting layer of an organic electroluminescent device, and an organic electroluminescent compound which has a remarkably improved driving voltage characteristic, Emitting device.

An organic light emitting phenomenon is a phenomenon that converts electric energy into light energy by using an organic material. An organic electroluminescent device using an organic light emitting phenomenon usually has a structure including an anode, an anode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic electroluminescent device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, . When a voltage is applied between the two electrodes in the structure of the organic electroluminescent device, holes are injected into the anode, electrons are injected into the organic layer, and excitons are formed when injected holes and electrons meet. When it falls back to the ground state, the light comes out. Such an organic electroluminescent device is known to have properties such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

Materials used as an organic material layer in an organic electroluminescent device can be classified into a light emitting material and a charge transporting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. In addition, the luminescent material can be classified into blue, green and red luminescent materials and yellow and orange luminescent materials necessary for realizing a better natural color depending on the luminescent color.

On the other hand, when only one material is used as the light emitting material, there arises a problem that the maximum light emitting wavelength shifts to a long wavelength due to intermolecular interaction, the color purity drops, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system may be used as a light emitting material in order to increase the efficiency of light emission through the light emitting layer.

In order for the organic electroluminescent device to sufficiently exhibit the above-described excellent characteristics, materials constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material are supported by a stable and efficient material However, the development of stable and efficient organic material layer materials for organic light emitting devices has not yet been sufficiently developed. Therefore, development of new materials is continuously required, and the necessity of developing such materials is the same in other organic electronic devices described above.

As a blue light emitting material, US Pat. No. 7053255 discloses a blue light emitting compound having a diphenyl anthracene structure and an aryl group substituted at the terminal thereof, and an organic electroluminescent device using the blue light emitting compound, but has a problem in that the light emitting efficiency and brightness are not sufficient . On the other hand, US Pat. No. 7233019 and Korean Patent Laid-Open Publication No. 2006-0006760 disclose an organic electroluminescent device using a substituted pyrene compound. However, since the color purity of blue is low, a deep blue It is difficult to realize a full-color full-color display.

The present invention provides a novel organic electroluminescent compound which can be used as a host compound or a dopant compound in a light emitting layer of an organic electroluminescent device to realize excellent luminescent characteristics and an organic electroluminescent device including the same.

In order to solve the above-described problems, the present invention provides an organic light-emitting compound represented by the following Chemical Formula 1 and an organic electroluminescent device including the same.

[Chemical Formula 1]

The specific structure and substituent of the organic luminescent compound according to the formula 1 will be described later.

The organic electroluminescent device employing the organic electroluminescent compound according to the present invention in the electroluminescent layer can be used for various display devices because it can realize more improved luminous efficiency and long life characteristics than the device using the conventional blue electroluminescent material .

1 to 5 are cross-sectional views illustrating the structure of an organic electroluminescent device according to an embodiment of the present invention.

Hereinafter, the present invention will be described more specifically.

The present invention relates to a novel organic luminescent compound represented by the following formula (1).

[Chemical Formula 1]

In the above formula (1)

X ₁ And X ₂ are the same or different and are each independently a single bond or any one selected from CR ₅ R ₆ , NR ₇ , SiR ₈ R ₉ , Ge R ₁₀ R ₁₁ , PR ₁₂ , O, S and Se.

R, R ₁ to R ₄ And R ₅ to R ₁₂ each independently represent hydrogen, deuterium, cyano, halogen, amino, thiol, hydroxyl, nitro, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted 3 A substituted or unsubstituted C1 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C1 to C50 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, A substituted or unsubstituted C 5 -C 50 aryl group, a substituted or unsubstituted C 3 -C 30 cycloalkyl, a substituted or unsubstituted C 6 -C 30 cycloalkyl, 2 to 50 heteroaryl groups and substituted or unsubstituted silyl groups.

m is an integer of 0 to 4, and when m is 2 or more, plural Rs may be the same or different from each other.

The above R, R ₁ to R ₄ And R ₅ to R ₁₂ may each be further substituted with one or more substituents, and the at least one substituent is selected from the group consisting of deuterium, cyano, halogen, amino, thiol, , A halogenated alkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, an alkoxy group having 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, And an arylsilyl group having 1 to 24 carbon atoms.

The above R, R ₁ to R ₄ And R ₅ to R ₁₂ and substituents thereof may be bonded to each other or may be connected to adjacent substituents to form a monocyclic or polycyclic ring of an alicyclic or aromatic group and may form a monocyclic or polycyclic ring of the formed alicyclic or aromatic monocyclic or polycyclic ring May be substituted with any one or more heteroatoms selected from N, S and O.

At least one of R ₁ to R ₄ is represented by the following formula (1).

[Structural formula 1]

In the structural formula 1,

L ₁ is selected from the group consisting of a single bond, a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted arylene group having 5 to 50 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms.

n is an integer of 1 to 4, and when n is 2 or more, a plurality of L ₁ may be the same or different from each other.

Ar ₁ and Ar ₂ are the same or different from each other, and each independently selected from a substituted or unsubstituted aryl group having 5 to 50 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms.

Ar ₁ and Ar ₂ may be bonded to each other or may be connected to adjacent substituents to form a single alicyclic or aromatic ring or polycyclic ring, and the carbon atom of the alicyclic or aromatic monocyclic or polycyclic ring may be N, S, Lt; / RTI > may be substituted with any one or more heteroatoms selected from < RTI ID = 0.0 >

p is an integer of 1 to 3, and when p is 2 or more, plural * - () may be the same or different from each other.

Wherein L _1, Ar ₁ and Ar ₂ are each further may be substituted, wherein at least one substituent at least one substituent is heavy hydrogen, a cyano group, a halogen group, an amino group, a thiol group, a hydroxy group, a nitro group, from 1 to 24 carbon atoms A halogenated alkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms having 1 to 24 carbon atoms And an arylsilyl group having 1 to 24 carbon atoms.

In the present invention, examples of the substituents will be specifically described below, but the present invention is not limited thereto.

In the present invention, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, Ethyl, propyl, isopropyl, n-butyl, isobutyl, isobutyl, isobutyl, A tert-butyl group, a tert-butyl group, a 2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, Ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , Isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group and the like, but are not limited thereto.

In the present invention, the alkoxy group may be linear or branched. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably in the range of 1 to 30, which does not cause steric hindrance. Specific examples thereof include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an i-propyloxy group, a n-butoxy group, an isobutoxy group, a tert- , Neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n- , A benzyloxy group, a p-methylbenzyloxy group, and the like, but are not limited thereto.

In the present invention, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples include a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2-yl group, But are not limited to, - (naphthyl-1-yl) vinyl-1-yl group, 2,2-bis (diphenyl-1-yl) vinyl-1-yl group, stilbenyl group, styrenyl group and the like.

In the present invention, the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 60. [ Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group and a stilbene group. Examples of the polycyclic aryl group include a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, , A chlorenyl group, a fluorenyl group, an acenaphthacenyl group, a triphenylene group, and a fluororanthrene group, but the scope of the present invention is not limited to these examples.

In the present invention, the heterocyclic group is a heterocyclic group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, , An indole group, a carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a dibenzofurancyl group, a phenanthroline group, An isothiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group and the like, but is not limited thereto.

In the present invention, the aryl group in the aryloxy group, arylthioxy group, arylsulfoxy group and aralkylamine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, an m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a ptert- Anthryloxy group, 2-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, Anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group and the like. Examples of the arylthioxy group include phenylthioxy group, 2- A 4-tert-butylphenyloxy group, and the like. Examples of the arylsulfoxy group include benzene sulfoxy group and p-toluenesulfoxy group. However, the present invention is not limited thereto.

In the present invention, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and specifically includes cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, Methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclo An octyl group, and the like, but are not limited thereto.

In the present invention, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present invention, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

Specific examples of the arylamine group include a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 3-methylphenylamine group, a 4-methylnaphthylamine group, But are not limited to, an amine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a carbazole group and a triphenylamine group.

In the present invention, the silyl group is specifically exemplified by trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, But are not limited thereto.

In the present invention, the heteroaryl group in the heteroarylamine group can be selected from the examples of the above-mentioned heterocyclic group.

In the present invention, the alkyloxy group in the alkylthio group and the alkyl group in the alkylsulfoxy group are the same as the aforementioned alkyl groups. Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group. Examples of the alkylsulfoxy group include a mesyl group, an ethylsulfoxy group, a propylsulfoxy group, But are not limited thereto.

In the present invention, the "substituted or unsubstituted" means a group selected from the group consisting of deuterium, halogen, nitrile, nitro, hydroxy, alkyl, cycloalkyl, , An arylsulfoxy group, an alkenyl group, a silyl group, a boron group, an alkylamine group, an aralkylamine group, an arylamine group, an aryl group, a fluorenyl group, a carbazole group and at least one of N, O and S atoms Substituted or unsubstituted with at least one substituent in the heterocyclic group.

In the present invention, the substituted arylene group means a phenyl group, a biphenyl group, a naphthalene group, a fluorenyl group, a pyrenyl group, a phenanthrenyl group, a perylene group, a tetracenyl group. Anthracenyl group and the like are substituted with other substituents.

In the present invention, the substituted heteroarylene group includes a pyridyl group, a thiophenyl group, a triazine group, a quinoline group, a phenanthroline group, an imidazole group, a thiazole group, an oxazole group, a carbazole group and condensed heterocyclic groups, Such as a benzoquinoline group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzzcarbazole group, a dibenzothiophenyl group, a dibenzofurane group and the like are substituted with other substituents.

The organic electroluminescent compound according to the present invention represented by Formula 1 can be used in various organic layers of organic electroluminescent devices due to its structural specificity, and can be preferably used as a host compound or a dopant compound in a light emitting layer.

Specific examples of the organic luminescent compound that may be employed as the host compound or the dopant compound of the light emitting layer represented by Formula 1 according to the present invention include, but are not limited to, the following compounds.

An organic luminescent compound having the intrinsic characteristics of the substituent introduced by introducing various substituents into the core structure having the above structure can be synthesized. For example, a substance that meets the requirements of each organic material layer can be manufactured by introducing a substituent used in a hole injecting layer material, a hole transporting layer material, and an electron transporting layer material used in manufacturing an organic electroluminescent device into the structure.

In particular, the organic electroluminescent compound represented by Formula 1 according to the present invention has excellent characteristics in terms of efficiency at the time of adoption, driving voltage, and life span in a light emitting layer of an organic electroluminescent device by introducing a substituent into the characteristic core structure, It is confirmed that the organic electroluminescent device can be realized.

The compound of the present invention can be applied to a device according to a conventional method of manufacturing an organic electroluminescent device. The organic electroluminescent device according to one embodiment of the present invention may have a structure including a first electrode, a second electrode and an organic material layer disposed therebetween, and the organic electroluminescent compound according to the present invention may be used for an organic material layer And can be manufactured using conventional device manufacturing methods and materials.

The organic material layer of the organic electroluminescent device according to the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. However, it is not limited to this and may include a smaller number of organic layers.

Therefore, in the organic electroluminescent device of the present invention, the organic material layer may be a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron injecting layer, a layer simultaneously injecting and transporting holes, a layer simultaneously performing electron injection and electron transporting, And one or more of the layers may include a compound represented by the formula 1. Preferably, the organic luminescent compound according to the present invention is a host or a dopant substance in the luminescent layer .

When the compound represented by the formula (1) is contained as an dopant in the light emitting layer, the dopant content may be generally selected in the range of about 0.01 to about 20 parts by weight based on 100 parts by weight of the host. In addition, a host or a dopant compound other than the organic light emitting compound represented by Formula 1 may be contained, and the content thereof is the same as above.

The organic electroluminescent device according to the present invention may further comprise an organic light emitting compound represented by the following formula (2), wherein the organic light emitting compound represented by the following formula (2) has a hole transporting layer, In the layer to be formed.

(2)

In the above formula (2)

X is the same or different and is each independently a single bond or any one of CR _a R _b , NR _c , SiR _d R _e , O and S.

Each of R _a to R _e is independently selected from the group consisting of hydrogen, deuterium, cyano, halogen, amino, thiol, hydroxyl, nitro, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C3- A substituted or unsubstituted C1 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, A substituted or unsubstituted aryl group having 5 to 50 carbon atoms in which at least one of the substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms is fused, a substituted or unsubstituted C2 to C30 cycloalkyl, To 50 heteroaryl groups and substituted or unsubstituted silyl groups.

R _a to R _e each may be further substituted with one or more substituents, and the one or more substituents may be deuterium, a cyano group, a halogen group, an amino group, a thiol group, a hydroxy group, a nitro group, A halogenated alkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms and an alkylsilyl group having 1 to 24 carbon atoms To 24 arylsilyl groups.

The R _a to R _e and substituents thereof may be bonded to each other or may be connected with adjacent substituents to form a single alicyclic or aromatic ring or polycyclic ring. The carbon atom of the formed alicyclic or aromatic monocyclic or polycyclic ring may be a N, S and O. The term " heteroaryl "

A and B are the same or different from each other, and each independently is characterized by being represented by the following structural formula (1).

[Structural formula 1]

In the structural formula 1,

In the organic compound layer having such a multilayer structure, the compound represented by the formula (1) may be used in combination with a light emitting layer, a layer that simultaneously transports holes and holes, a layer that simultaneously transports light and emits light, .

For example, the structure of an organic electronic device according to the present invention is illustrated in Figs.

1 shows an organic electronic device in which an anode 2, a hole injecting layer 3, a hole transporting layer 4, a light emitting layer 5, an electron transporting layer 6 and a cathode 7 are sequentially laminated on a substrate 1 Structure is illustrated. In this structure, the compound represented by the formula (1) may be included in the hole injection layer (3), the hole transport layer (4), the light emitting layer (5) or the electron transport layer (6).

2 shows the structure of an organic electronic device in which an anode 2, a hole injecting layer 3, a hole transporting layer 4, a light emitting layer 5 and a cathode 7 are sequentially laminated on a substrate 1. In such a structure, the compound represented by the formula (1) may be included in the hole injection layer (3), the hole transport layer (4), or the electron transport layer (6).

3 illustrates the structure of an organic electronic device in which an anode 2, a hole transporting layer 4, a light emitting layer 5, an electron transporting layer 6, and a cathode 7 are sequentially stacked on a substrate 1. In such a structure, the compound represented by the formula (1) may be included in the hole transport layer (4), the light emitting layer (5), or the electron transport layer (6).

4 illustrates the structure of an organic electronic device in which an anode 2, a light emitting layer 5, an electron transport layer 6, and a cathode 7 are sequentially laminated on a substrate 1. In FIG. In such a structure, the compound represented by the formula (1) may be included in the light-emitting layer (5) or the electron-transporting layer (6).

5 illustrates the structure of an organic electronic device in which an anode 2, a light-emitting layer 5, and a cathode 7 are sequentially stacked on a substrate 1. As shown in Fig. In such a structure, the compound represented by the formula (1) may be included in the luminescent layer (5).

For example, the organic electroluminescent device according to the present invention can be manufactured by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a metal oxide or a conductive metal oxide on the substrate, An anode is formed by depositing an alloy on the anode, and an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer is formed on the anode, and then a substance usable as a cathode is deposited thereon.

In addition to such a method, an organic electroluminescent device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate. The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic material layer may be formed using a variety of polymer materials by a solvent process such as a spin coating process, a dip coating process, a doctor blading process, a screen printing process, an inkjet printing process or a thermal transfer process, Layer.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO) metal oxides, ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT) , Conductive polymers such as polypyrrole and polyaniline, but are not limited thereto.

The negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or an alloy thereof; a multilayer such as LiF / Al or LiO ₂ / Structural materials, and the like, but are not limited thereto.

As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene, quinacridone-based organic materials, perylene-based organic materials, Anthraquinone, polyaniline and a polythiophene-based conductive polymer, but are not limited thereto.

As the hole transporting material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high mobility to holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having a high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ), carbazol-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzthiazole and A benzimidazole-based compound, a poly (p-phenylene vinylene) (PPV) -based polymer, a spiro compound, polyfluorene, rubrene, and the like.

As the electron transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is highly mobile, is suitable. Specific examples thereof include, but are not limited to, an Al complex of 8-hydroxyquinoline, a complex containing Alq ₃ , an organic radical compound, and a hydroxyflavone-metal complex.

The organic electroluminescent device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

In addition, the organic electroluminescent compound according to the present invention can act on a principle similar to that applied to an organic electroluminescent device in an organic electronic device including an organic solar cell, an organophotoreceptor, an organic transistor and the like.

Hereinafter, preferred embodiments of the present invention will be described in order to facilitate understanding of the present invention. However, the following examples are intended to illustrate the invention and are not intended to limit the scope of the invention.

Example 1: Synthesis of compound 1

(One) Manufacturing example 1: Synthesis of intermediate 1-1

Bis (pinacolato) dibron (6.0 g, 0.024 mol), PdCl ₂ (dppf) (0.4 g, 0.0005 mol), potassium acetate (2.8 g, 0.020 mol) were added to 1,6-dibromo-pyrene ), 120 mL of 1,4-dioxane was added, and the reaction was carried out at 95 ° C for 24 hours. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and purified by column (n-hexane: MC) 3.2 g (71% yield). (m / z = 456)

(2) Manufacturing example 2: Synthesis of intermediate 1-2

To the intermediate 1-1 (4.6 g, 0.010 mol) was added ethyl 2-bromobenzoate (5.0 g, 0.022 mol), tetrabutyl-ammonium bromide (6.4 g, 0.020 mol), potassium carbonate (5.6 g, 0.040 mol), Pd ₃ ) ₄ (1.0 g, 0.0010 mol) was added 200 mL of TOL, stirred, and reacted at 90 ° C for 12 hours. After completion of the reaction, the reaction mixture was cooled, and the mixture was subjected to column purification (n-hexane: EA) to obtain 4.5 g of Intermediate 1-2 (yield 90%). (m / z = 500)

(3) Manufacturing example 3: Synthesis of intermediate 1-3

Intermediate 1-2 (5.0 g, 0.010 mol) was added to 50 mL of methanesulfonic acid, the temperature was raised to 75 ° C, and the mixture was stirred for 4 hours. After completion of the reaction, the reaction mixture was cooled, the reaction mixture was separated, and the filtrate was dried with MgSO ₄ under reduced pressure to obtain 3.5 g (85%) of Intermediate 1-3 (m / z = 408)

(4) Manufacturing example 4: Synthesis of compound 1

1-Bromo-2-phenoxybenzene (7.5 g, 0.030 mol) was dissolved in 70 mL of THF, and the reaction temperature was lowered to -78 ° C. and 2.5 M of BuLi was slowly dropped 5 mL, followed by stirring for 1 hour. Intermediate 1-3 (4.1 g, 0.010 mol) was dissolved in 40 mL of THF, and the mixture was slowly added dropwise thereto. The mixture was stirred at room temperature for 12 hours. After the reaction was completed, the reaction mixture was extracted with distilled water and MC, dried under reduced pressure with MgSO ₄ , and dissolved in 50 mL of acetic acid. Then, 7 mL of MgSO ₄ was dropped and refluxed. After the reaction was completed, the reaction mixture was extracted with distilled water and MC, and the resulting solid was subjected to column purification (n-hexane: EA) to obtain 3.8 g (53%) of Compound 1.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.09 / d, 7.86 / d, 7.61 / d, 7.44 / m, 7.24 / m) 4H (7.71 / d, 7.22 / m, 7.21 / d, 7.19 / d, 7.05 / m)

LC / MS: m / z = 711 [(M + 1) ^< ^{+ &}

Example 2: Synthesis of compound 2

(One) Manufacturing example 1: Synthesis of intermediate 2-1

After dissolving 1-benzyl-2-bromobenzene (2.5 g, 0.010 mol) in 50 mL of DMSO, sodium tert-butoxide (4.8 g, 0.050 mol) was added at room temperature and the mixture was exchanged at 70 ° C for 15 minutes. Then, methyl iodide (7.3 g, 0.050 mol) was slowly dropped and stirred for 1 hour. After completion of the reaction, the reaction product was cooled, and the product was separated into H ₂ O: MC and column-purified (n-hexane: MC) to give 1.7 g (m / z = 275)

(2) Manufacturing example 2: Synthesis of Compound 2

Synthesis was conducted in the same manner as in Example 1 (4) using Intermediate 2-1 (8.3 g, 0.030 mol) and Intermediate 1-3 (4.1 g, 0.010 mol) Yield: 52%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.97 / d, 7.86 / d, 7.41 / d, 7.25 / m, 7.12 / m) 4H (7.71 / d, 1.72 / s) 8H (7.31 / d , 7.19 / m)

LC / MS: m / z = 763 [(M + 1) ^< ^{+ &}

Example 3: Synthesis of Compound 7

(One) Manufacturing example 1: Synthesis of Compound 7

Synthesis was conducted by the same method as in Example 1-Preparation Example (4) using Intermediate 2-1 (8.3 g, 0.030 mol) and 2-bromobiphenyl (2.3 g, 0.010 mol) 46%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.09 / d, 7.86 / d, 7.61 / d, 7.44 / m, 7.35 / d, 7.35 / s, 7.24 / m) 4H (7.75 / d, 7.71 / d, 7.19 / m, 7.16 / m)

LC / MS: m / z = 679 [(M + 1) ^< ^{+ &}

Example 4: Compound 30 Synthesis

(One) Manufacturing example 1: Synthesis of Intermediate 4-1

Under nitrogen atmosphere for 2-chloroaniline (1.3 g, 0.010 mol), bromobenzene (1.6 g, 0.010 mol), Pd (dba) 3 (0.1 g, 0.001 mol), P (t-Bu) 3 (0.04 g, 0.0002 mol) , STBT (2.9 g, 0.030 mol), and the mixture was stirred under reflux. After completion of the reaction, the reaction mixture was subjected to layer separation with H ₂ O: EA and then subjected to column purification (N-HEXANE: MC) to obtain 1.5 g (yield: 62%) of <Intermediate 4-1>. (m / z = 248)

(2) Manufacturing example 2: Synthesis of intermediate 4-2

Intermediate 4-2 was synthesized by the same method as in Preparation Example 4 (4) using Intermediate 4-1 (7.4 g, 0.030 mol) and 2-bromobiphenyl (2.3 g, 0.010 mol) (Yield: 50%). (m / z = 708)

(3) Manufacturing example 3: Synthesis of compound 30

Synthesis was conducted in the same manner as in Example 4 (1), except that Intermediate 4-2 (7.1 g, 0.010 mol) and (4-bromophenyl) trimethylsilane (4.6 g, 0.020 mol) (Yield: 73%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.09 / d, 7.86 / d, 7.61 / d, 7.44 / m, 7.24 / m) 4H (7.71 / d, 7.15 / d, 7.01 / m, 6.98 / d, 6.69 / m, 6.61 / d, 6.51 / d) 6H (0.25 / s)

LC / MS: m / z = 1006 [(M + 1) ^< ^{+ &}

Example 5: Compound 38 Synthesis

(One) Manufacturing example 1: Synthesis of intermediate 5-1

Tig (tetraiodoglycoluril) (6.5 g, 0.010 mol) and acetic acid (10 mL) were added to 100 mL of dioxane, and the mixture was stirred at 20 ° C for 20 minutes (yield: 82%). The isomer was recrystallized using Chlorobenzene to obtain 0.6 g (Intermediate 5-1) (yield: 15%). (m / z = 456)

(2) Manufacturing example 2: Synthesis of Intermediate 5-2

100 mL of DMF was added to Bromine (3.2 g, 0.020 mol) in Intermediate 5-1 (4.6 g, 0.010 mol) and the mixture was reacted at 20 ° C for 8 hours with stirring.

After completion of the reaction H ₂ 0: After phase separation with ethyl acetate and column purification: by (n-Hexane MC) to afford 2.5 g (41%) of <Intermediate 5-2> (m / z = 613 ).

(3) Manufacturing example 3: Synthesis of intermediate 5-3

Intermediate 5-3 was synthesized by the same procedure as in Example 1-Preparation Example (2), except that isopropylboronic acid (2.1 g, 0.024 mol) was added to Intermediate 5-2 (6.1 g, 0.010 mol) 65%). (m / z < / RTI > = 446)

(4) Manufacturing example 4: Synthesis of intermediate 5-4

Intermediate 5-4 was synthesized by the same method as in Example 1 (1) except that Intermediate 5-3 (6.0 g, 0.010 mol) and bis (pinacolato) dibron (6.0 g, 0.024 mol) g (yield: 62%). (m / z = 540)

(5) Manufacturing example 5: Synthesis of intermediate 5-5

Intermediate 5-5 was synthesized in the same manner as in Example 1 (2) except that Intermediate 5-4 (5.4 g, 0.010 mol) and ethyl 2-bromobenzoate (5.0 g, 0.022 mol) (Yield: 62%). (m / z = 584)

(6) Manufacturing example 6: Synthesis of intermediate 5-6

Intermediate 5-5 (5.8 g, 0.010 mol) was synthesized by the same method as in Example 1- (3) to give 4.1 g (yield 83%) of Intermediate 5-6. (m / z = 492)

(7) Manufacturing example 7: Synthesis of Compound 38

The compound 5 was synthesized by the same method as in Example 1 (4) using Intermediate 5-6 (14.8 g, 0.030 mol) and 1-bromo-2-phenoxybenzene (2.5 g, 0.010 mol) 3.3 g (yield: 42%) was obtained.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.09 / d, 7.86 / s, 7.61 / d, 7.58 / s, 7.44 / m, 7.24 / m, 2.87 / s) 4H (7.22 / m, 7.21 / d, 7.19 / d, 7.05 / m, 1.33 / s)

LC / MS: m / z = 795 [(M + 1) ^< ^{+ &}

Example 6: Compound 86 Synthesis

(One) Manufacturing example 1: Synthesis of intermediate 6-1

Intermediate 6-1 was synthesized by the same method as in Preparation Example 4 (4) using Intermediate 5-6 (14.8 g, 0.030 mol) and Intermediate 4-1 (2.5 g, 0.010 mol) g (yield: 45%). (m / z = 793)

(2) Manufacturing example 2: Synthesis of Compound 86

Synthesis was conducted in the same manner as in Example 4 (1), except that 4-bromobenzonitrile (3.6 g, 0.020 mol) was added to intermediate 6-1 (7.9 g, 0.010 mol) %).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.09 / d, 7.86 / d, 7.61 / d, 7.58 / s, 7.44 / m, 7.24 / m, 2.87 / s) 4H (7.39 / d, 7.01 / m, 6.98 / d, 6.81 / d, 6.69 / m, 6.51 / d, 1.33 / s)

LC / MS: m / z = 996 [(M + 1) ^< ^{+ &}

Example 7: Compound 94 Synthesis

(One) Manufacturing example 1: Synthesis of Intermediate 7-1

(pinacolato) dibron (3.0 g, 0.012 mol) was added to bromotrimethylsilane (1.5 g, 0.010 mol) in the same manner as in Example 1 (1) 73%). (m / z = 200)

(2) Manufacturing example 2: Synthesis of intermediate 7-2

Intermediate 7-1 (4.8 g, 0.024 mol) was added to Intermediate 5-2 (6.1 g, 0.010 mol) and the same procedure as in Example 1 (2) (Yield: 63%). (m / z = 506)

(3) Manufacturing example 3: Synthesis of intermediate 7-3

Intermediate 7-3 was synthesized by the same method as in Preparation Example (1) of Example 1, except that bis (pinacolato) dibron (6.0 g, 0.024 mol) was added to Intermediate 7-2 (5.1 g, 0.010 mol) g (yield: 72%). (m / z = 600)

(4) Manufacturing example 4: Synthesis of Intermediate 7-4

(5.5 g, 0.024 mol) was added to 1,3-dibromo-5-chlorobenzene (6.0 g, 0.010 mol) and the reaction was conducted in the same manner as in Example 1- 4> (4.7 g, yield 73%). (m / z = 644)

(5) Manufacturing example 5: Synthesis of intermediate 7-5

Intermediate 7-4 (6.4 g, 0.010 mol) was synthesized by the same method as in Example 1- (3) to give 4.4 g (yield 80%) of Intermediate 7-5. (m / z = 552)

(6) Manufacturing example 6: Synthesis of Compound 94

Synthesis was conducted in the same manner as in Example 1 (4) using Intermediate 7-5 (5.5 g, 0.030 mol) and (2-bromophenyl) (phenyl) sulfane (2.3 g, 0.010 mol) (Yield: 49%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.09 / d, 7.93 / s, 7.86 / d, 7.61 / d, 7.44 / m, 7.24 / m) 4H (7.65 / d, 7.33 / m, 7.07 / m, 7.03 / s) 6H (0.25 / s)

LC / MS: m / z = 888 [(M + 1) ^< ^{+ &}

Example 8: Compound 120 Synthesis

(One) Manufacturing example 1: Synthesis of Intermediate 8-1

Synthesis was conducted in the same manner as in Example 4 (1) except that 4-bromodibenzo [b, d] thiophene (2.6 g, 0.010 mol) was added to 3,5-dimethylaniline (1.2 g, 0.010 mol) 2.3 g (yield 75%) of 8-1 (m / z = 303)

(2) Manufacturing example 2: Synthesis of Intermediate 8-2

Intermediate 8-2 (6.0 g, 0.020 mol) was added to Intermediate 5-2 (6.1 g, 0.010 mol) and the same procedure as in Example 4 (1) (Yield: 73%). (m / z < / RTI > = 962)

(3) Manufacturing example 3: Synthesis of Intermediate 8-3

<Intermediate 8-3> was synthesized in a similar manner as in Example 1 (7) (7.6 g, 0.024 mol) by adding bis (pinacolato) dibron (6.0 g, 0.024 mol) to Intermediate 8-2 g (yield: 72%). (m / z = 1056)

(4) Manufacturing example 4: Synthesis of Intermediate 8-4

Intermediate 8-4 was synthesized in the same manner as in Example 1- (2) except that Intermediate 8-3 (10.6 g, 0.010 mol) and ethyl 2-bromobenzoate (5.0 g, 0.022 mol) (Yield: 62%). (m / z = 1101)

(5) Manufacturing example 5: Synthesis of intermediate 8-5

Intermediate 8-4 (11.0 g, 0.010 mol) was synthesized in the same manner as in Example 1- (3) to give 8.0 g (79% yield) of Intermediate 8-5. (m / z = 1009)

(6) Manufacturing example 6: Synthesis of Compound 120

The compound 8 was synthesized by the same method as in Example 1 (4) using Intermediate 8-5 (30.3 g, 0.030 mol) and 2-bromobiphenyl (2.3 g, 0.010 mol) 38%).

M, 7.44 / m (1 H-NMR (200MHz, CDCl ₃ ):? Ppm, 2H (8.45 / d, 8.09 / d, 7.98 / d, 7.86 / s, 7.81 / d, 7.61 / d, 7.52 / M, 7.16 / m, 6.36 / s, 2.34 / s, 7.35 / d, 7.35 / s, 7.27 / m, 7.24 / m, 6.91 / s, 6.86 / )

LC / MS: m / z = 1282 [(M + 1) ^< ^{+ &}

Example 9: Synthesis of compound 121

(One) Manufacturing example 1: Synthesis of intermediate 9-1

Synthesis was conducted in the same manner as in Example 4 (1) except that 4-bromodibenzo [b, d] furan (2.5 g, 0.010 mol) was added to 3,5-dimethylaniline (1.2 g, 0.010 mol) 9-1> 2.0 g (yield 70%). (M / z = 287)

(2) Manufacturing example 2: Synthesis of intermediate 9-2

Intermediate 5-2 (6.1 g, 0.010 mol) was synthesized in the same manner as in Example 4 (1) except that Intermediate 9-1 (5.7 g, 0.020 mol) was added, and 6.8 g (Yield: 73%). (m / z = 930)

(3) Manufacturing example 3: Synthesis of intermediate 9-3

Intermediate 9-3 was synthesized by the same method as in Preparation Example 1 (1) except that bis (pinacolato) dibron (6.0 g, 0.024 mol) was added to Intermediate 9-2 (9.3 g, 0.010 mol) g (yield: 73%). (m / z = 1024)

(4) Manufacturing example 4: Synthesis of intermediate 9-4

Intermediate 9-4 was synthesized in the same manner as in Example 1 (2) except that Intermediate 9-3 (10.2 g, 0.010 mol) and ethyl 2-bromobenzoate (5.0 g, 0.022 mol) (Yield: 60%). (m / z = 1069)

(5) Manufacturing example 5: Synthesis of intermediate 9-5

Intermediate 9-4 (10.7 g, 0.010 mol) was synthesized in the same manner as in Example 1- (3) to give 8.1 g (83% yield) of Intermediate 9-5. (m / z = 977)

(6) Manufacturing example 6: Synthesis of Compound 121

Synthesis was conducted in the same manner as in Example 1 (4) using intermediate 9-5 (29.3 g, 0.030 mol) and 2-bromobiphenyl (2.3 g, 0.010 mol) 41%).

M, 7.44 / m (1 H-NMR (200MHz, CDCl ₃ ):? Ppm, 2H (8.45 / d, 8.09 / d, 7.98 / d, 7.86 / s, 7.81 / d, 7.61 / d, 7.52 / M, 7.16 / m, 6.36 / s, 2.34 / s, 7.35 / d, 7.35 / s, 7.28 / d, 7.24 / m, 6.91 / s, 6.86 / )

LC / MS: m / z = 1250 [(M + 1) ^< ^{+ &}

Example 10: Compound 123 Synthesis

(One) Manufacturing example 1: Synthesis of Compound 123

Compound 10 was synthesized by the same method as Preparation Example (4) using Intermediate 9-5 (29.3 g, 0.030 mol) and 1-bromo-2-phenoxybenzene (2.5 g, 0.010 mol) 5.3 g (yield 41%) was obtained.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.09 / d, 7.89 / d, 7.86 / d, 7.66 / d, 7.61 / s, 7.44 / m, 7.38 / m, 7.32 / m, 7.25 / d (7.22 / m, 7.21 / d, 7.09 / d, 7.05 / m, 6.36 / s, 2.34 /

LC / MS: m / z = 1282 [(M + 1) ^< ^{+ &}

Example 11: Compound 127 Synthesis

(One) Manufacturing example 1: Synthesis of intermediate 11-1

Synthesis was conducted in the same manner as in Example 4 (1) except that 4-aminobenzonitrile (1.2 g, 0.010 mol) was added to 1-bromo-4-tert-butylbenzene (2.1 g, 0.010 mol) (2.1 g, yield 82%). (m / z = 250)

(2) Manufacturing example 2: Synthesis of intermediate 11-2

Intermediate 5-2 (6.1 g, 0.010 mol) was synthesized in the same manner as in Example 4 (1) except that Intermediate 11-1 (5.0 g, 0.020 mol) was added and 6.2 g (Yield: 73%). (m / z = 856)

(3) Manufacturing example 3: Synthesis of intermediate 11-3

Intermediate 11-3 was synthesized by the same method as in Preparation Example (1) of Example 1, except that bis (pinacolato) dibron (3.0 g, 0.012 mol) was added to Intermediate 11-2 (8.6 g, 0.010 mol) g (yield 66%). (m / z = 950)

(4) Manufacturing example 4: Synthesis of intermediate 11-4

Intermediate 11-4 was synthesized in the same manner as in Example 1 (2), except that 6.0 g of Intermediate 11-4 (9.5 g, 0.010 mol) and ethyl 2-bromobenzoate (5.0 g, 0.022 mol) (Yield: 60%). (m / z < / RTI > = 996)

(5) Manufacturing example 5: Synthesis of intermediate 11-5

Intermediate 11-4 (10.0 g, 0.010 mol) was synthesized in the same manner as in Example 1- (3) to give 7.0 g (yield 78%) of Intermediate 11-5. (m / z = 903)

(6) Manufacturing example 6: Synthesis of Compound 11

Compound 11 was synthesized by the same method as Preparation Example (4) using Intermediate 11-5 (27.1 g, 0.030 mol) and 1-bromo-2-phenoxybenzene (2.5 g, 0.010 mol) 5.8 g (yield: 48%) was obtained.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.09 / d, 7.61 / d, 7.44 / m, 7.24 / m, 6.91 / s) 4H (7.39 / d, 7.22 / m, 7.21 / d, 7.19 / d, 7.05 / d, 7.01 / d, 6.81 / d, 6.55 / d) 6H (1.35 / s)

LC / MS: m / z = 1208 [(M + 1) ^< ^{+ &}

device Example 1: Compound 1 The light- Neon blue As a host material Organic electroluminescent device Produce

The ITO transparent electrode (anode) was subjected to ultrasonic cleaning for 5 minutes in isopropyl-alcohol, followed by UV ozone cleaning for 30 minutes. The cleaned glass substrate on which the transparent electrode line was formed was mounted on the substrate holder of the vacuum evaporation apparatus. First, CuPc (30 nm) was deposited as a hole injecting material on the side where the transparent electrode line was formed to cover the transparent electrode. Compound (0) (80 nm) was deposited thereon with a hole transporting material, and Compound 1: Compound B was deposited at a mass ratio of 20: 1 to form a light emitting layer with a film thickness of 20 nm. After that, Alq ₃ (25 nm) and LiF (1 nm) were formed as an electron injecting material, and then a negative electrode was formed with Al (80 nm).

device Example 2 to 4

The organic electroluminescent devices of the device embodiments 2 to 4 were fabricated in the same manner as in the device example 1 except that the compound described in the following Table 1 was used instead of the compound 1.

device Comparative Example One

The organic light emitting diode device for the comparative example was fabricated in the same manner except that the compound A, which is generally used as a fluorescent host material, was used instead of the compound prepared by the invention in the device structure of the embodiment.

device Example 5: Compound 5 The light- Neon blue Dopant Organic by material I'm Based light emitting device manufacturing

The ITO transparent electrode (anode) was subjected to ultrasonic cleaning for 5 minutes in isopropyl-alcohol, followed by UV ozone cleaning for 30 minutes. The cleaned glass substrate on which the transparent electrode line was formed was mounted on the substrate holder of the vacuum evaporation apparatus. First, CuPc (30 nm) was deposited as a hole injecting material on the side where the transparent electrode line was formed to cover the transparent electrode. Compound (0) (80 nm) was deposited thereon with a hole transporting material, and Compound A: Compound 5 was deposited at a mass ratio of 20: 1 to form a light emitting layer with a thickness of 20 nm. After that, Alq ₃ (25 nm) and LiF (1 nm) were formed as an electron injecting material, and then a negative electrode was formed with Al (80 nm).

device Example 6 to 11

An organic electroluminescent device of each of the device embodiments 6 to 11 was fabricated in the same manner as in the device example 5, except that the compound described in the following Table 2 was used in place of the compound 5.

device Comparative Example 2

The organic light emitting diode device for the comparative example was fabricated in the same manner except that the compound B, which is generally used as a fluorescent dopant material instead of the compound prepared by the invention in the device structure of the embodiment, was used.

The structure of the compound used above is as follows.

[CuPc] [Compound 0]

[Compound A] [Compound B]

Hereinafter, the characteristics of the organic electroluminescent devices manufactured according to the device embodiments 1 to 11 and the device comparison examples 1 and 2 are shown in Table 1 and Table 2, respectively.

[Table 1]

[Table 2]

Measurement of driving voltage and luminous efficiency

After fixing the organic light emitting device (substrate size: 25 × 25 mm 2 / deposition area: 2 × 2 mm 2) made in the above to the IVL measurement set (CS-2000 + jig + IVL program), the current was increased by 1 mA / (Cd / m < 2 >), a driving voltage (V) and a luminous efficiency (cd / A) were measured and shown in Table 1 and Table 2, respectively. From the results of Examples and Comparative Examples and [Table 1] and [Table 2], it was found that the compound according to the present invention had better characteristics such as driving voltage and luminous efficiency than conventional blue fluorescent light emitting materials, Display elements, display elements, illumination, and the like.

Claims

An organic light-emitting compound represented by the following Formula 1:
[Chemical Formula 1]

In the above formula (1)
X ₁ And X ₂ are the same or different and are each independently a single bond or any one selected from CR ₅ R ₆ , NR ₇ , SiR ₈ R ₉ , Ge R ₁₀ R ₁₁ , PR ₁₂ , O, S and Se ;
R, R ₁ to R ₄ And R ₅ to R ₁₂ each independently represent hydrogen, deuterium, cyano, halogen, amino, thiol, hydroxyl, nitro, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted 3 A substituted or unsubstituted C1 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C1 to C50 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, A substituted or unsubstituted C 5 -C 50 aryl group, a substituted or unsubstituted C 3 -C 30 cycloalkyl, a substituted or unsubstituted C 6 -C 30 cycloalkyl, 2 to 50 heteroaryl groups and substituted or unsubstituted silyl groups;
m is an integer of 0 to 4, and when m is 2 or more, plural Rs are the same or different from each other;
The above R, R ₁ to R ₄ And R ₅ to R ₁₂ may each be further substituted with one or more substituents, and the at least one substituent is selected from the group consisting of deuterium, cyano, halogen, amino, thiol, , A halogenated alkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, an alkoxy group having 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, An arylsilyl group having 1 to 24 carbon atoms;
The above R, R ₁ to R ₄ And R ₅ to R ₁₂ and substituents thereof may be bonded to each other or may be connected to adjacent substituents to form a monocyclic or polycyclic ring of an alicyclic or aromatic group and may form a monocyclic or polycyclic ring of the formed alicyclic or aromatic monocyclic or polycyclic ring May be substituted with any one or more heteroatoms selected from N, S and O.

The method according to claim 1,
Wherein at least one of R ₁ to R ₄ is represented by the following formula 1:
[Structural formula 1]

In the structural formula 1,
L ₁ is selected from the group consisting of a single bond, a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted arylene group having 5 to 50 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms;
n is an integer of 1 to 4, and when n is 2 or more, a plurality of L ₁ are the same or different from each other;
Ar ₁ and Ar ₂ are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 5 to 50 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms;
Ar ₁ and Ar ₂ may be bonded to each other or may be connected to adjacent substituents to form a single alicyclic or aromatic ring or polycyclic ring, and the carbon atom of the alicyclic or aromatic monocyclic or polycyclic ring may be N, S, O, < / RTI >< RTI ID = 0.0 >
p is an integer of 1 to 3, and when p is 2 or more, plural * - (s) may be the same or different from each other;
Wherein L _1, Ar ₁ and Ar ₂ are each further may be substituted, wherein at least one substituent at least one substituent is heavy hydrogen, a cyano group, a halogen group, an amino group, a thiol group, a hydroxy group, a nitro group, from 1 to 24 carbon atoms A halogenated alkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms having 1 to 24 carbon atoms And an arylsilyl group having 1 to 24 carbon atoms.

The method according to claim 1,
The organic electroluminescent compound according to claim 1, wherein the organic electroluminescent compound is selected from the following compounds [1] to [133]:

1. An organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode,
Wherein at least one of the organic material layers comprises an organic light emitting compound represented by Formula 1 according to Claim 1.

5. The method of claim 4,
Wherein the organic material layer includes at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole transporting and hole transporting layer, an electron transporting layer, an electron injection layer,
Wherein at least one of the layers comprises an organic light-emitting compound represented by the formula (1).

6. The method of claim 5,
Wherein the light emitting layer comprises an organic light emitting compound represented by Formula 1 below.

The method according to claim 6,
Wherein the organic light emitting compound represented by Formula 1 is used as a host compound or a dopant compound in the light emitting layer.

8. The method of claim 7,
Wherein the light emitting layer further comprises at least one host compound or a dopant compound other than the organic light emitting compound represented by Formula 1 below.

5. The method of claim 4,
Wherein the organic material layer further comprises an organic light emitting compound represented by the following Formula 2 and the organic light emitting compound represented by the following Formula 2 is contained in a hole transporting layer or a layer that simultaneously performs hole injection and hole transporting functions The organic electroluminescent device comprising:
(2)

In the above formula (2)
X is the same or different and is each independently a single bond or any one of CR _a R _b , NR _c , SiR _d R _e , O and S;
Each of R _a to R _e is independently selected from the group consisting of hydrogen, deuterium, cyano, halogen, amino, thiol, hydroxyl, nitro, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C3- A substituted or unsubstituted C1 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, A substituted or unsubstituted aryl group having 5 to 50 carbon atoms in which at least one of the substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms is fused, a substituted or unsubstituted C2 to C30 cycloalkyl, To 50 heteroaryl groups and substituted or unsubstituted silyl groups;
R _a to R _e each may be further substituted with one or more substituents, and the one or more substituents may be deuterium, a cyano group, a halogen group, an amino group, a thiol group, a hydroxy group, a nitro group, A halogenated alkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms and an alkylsilyl group having 1 to 24 carbon atoms Lt; / RTI > to 24 arylsilyl groups;
The R _a to R _e and substituents thereof may be bonded to each other or may be connected with adjacent substituents to form a single alicyclic or aromatic ring or polycyclic ring. The carbon atom of the formed alicyclic or aromatic monocyclic or polycyclic ring may be a N, S and O; and R < 2 >
A and B are the same or different from each other, and each independently is represented by the following formula 1;
[Structural formula 1]

5. The method of claim 4,
Wherein at least one of the organic light emitting layers emitting red, green or blue light is further included in the organic material layer to emit white light.